I'm on Toad 18.104.22.168 - but this issue has been bugging me for quite a while.
In my project manager view I have an extensive set of links organized in folders and subfolders.
Whenever new files need to be added I use the 'refresh folder links' option.
Normally, this will add any new files to the bottom of the list,
so I request to have the folder's children sorted.
This sort sometimes fails to produce the correct order.
A repeated sort resolves the issue.
Still, it's strange the sort produces incorrect results on the first attempt.
Here's an example:
The file $upgrade_20161208.sql was added.
The list shown in the figure shows results after the first sort.
As you can see, the sort has moved the new file correctly after $upgrade_20161113.sql,
but at the same time the $upgrade_20160930 has been moved to an incorrect location.
Would you please give it a try and see if this reproduces on your side?